Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

Provided are a condensed cyclic compound and an organic light-emitting device including the same.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the benefit of Korean Patent Application No.10-2018-0072153, filed on Jun. 22, 2018, in the Korean IntellectualProperty Office, the disclosure of which is incorporated herein in itsentirety by reference.

BACKGROUND 1. Field

One or more embodiments relate to a condensed cyclic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that producefull-color images, and also have wide viewing angles, high contrastratios, short response times, and excellent characteristics in terms ofbrightness, driving voltage, and response speed, compared to devices inthe art.

An example of such organic light-emitting devices may include a firstelectrode disposed on a substrate, and a hole transport region, anemission layer, an electron transport region, and a second electrode,which are sequentially disposed on the first electrode. Holes providedfrom the first electrode may move toward the emission layer through thehole transport region, and electrons provided from the second electrodemay move toward the emission layer through the electron transportregion. Carriers, such as holes and electrons, recombine in the emissionlayer to produce excitons. These excitons transit from an excited stateto a ground state, thereby generating light.

SUMMARY

One or more embodiments provide a condensed cyclic compound and anorganic light-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

An aspect provides a condensed cyclic compound represented by Formula1-1 or 1-2:

In Formulae 1-1, 1-2, and 2,

X₁ and X₂ may each independently be selected from O, S, andSi(R₁₃)(R₁₄),

L₁, L₁₁, and L₁₂ may each independently be selected from *—O—*′, asubstituted or unsubstituted C₃-C₆₀ carbocyclic group, and a substitutedor unsubstituted C₁-C₆₀ heterocyclic group,

a1 may be an integer from 1 to 5,

a11 and a12 may each independently be an integer from 0 to 4,

Ar₁ and Ar₂ may each independently be selected from a substituted orunsubstituted C₃-C₆₀ carbocyclic group and a substituted orunsubstituted C₁-C₆₀ heterocyclic group,

R₁ to R₁₄ may each independently be selected from a group represented byFormula 2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂),—S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

at least one selected from R₅ to R₈ may be a group represented byFormula 2,

R₁ to R₄ do not include a carbazole group,

any two neighboring groups among R₁ to R₁₄ may optionally be linked toform a substituted or unsubstituted C₃-C₆₀ carbocyclic group or a C₁-C₆₀heterocyclic group,

at least one substituent of the substituted C₃-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₂-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, a terphenyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with a C₁-C₆₀ alkyl group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group, and

* and *′ each indicate a binding site to a neighboring atom.

Another aspect provides an organic light-emitting device including: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode andincluding an emission layer, wherein the organic layer includes at leastone of the condensed cyclic compound.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawings in which:

FIG. 1 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 2 is a schematic view of an organic light-emitting device accordingto another embodiment;

FIG. 3 is a schematic view of an organic light-emitting device accordingto another embodiment; and

FIG. 4 is a schematic view of an organic light-emitting device accordingto another embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list. A condensed cycliccompound according to an embodiment is represented by Formula 1-1 or1-2:

In Formulae 1-1 to 1-2 and 2, X₁ and X₂ may each independently beselected from O, S, and Si(R₁₃)(R₁₄).

In one embodiment, i) each of X₁ and X₂ may be O, ii) each of X₁ and X₂may be S, iii) X₁ may be O, and X₂ may be S or Si(R₁₃)(R₁₄), iv) X₁ maybe S, and X₂ may be O or Si(R₁₃)(R₁₄), V) X₁ may be S or Si(R₁₃)(R₁₄),and X₂ may be O, or vi) X₁ may be O or Si(R₁₃)(R₁₄), and X₂ may be S.

In Formulae 1-1 to 1-2 and 2, L₁, L₁₁, and L₁₂ may each independently beselected from *—O—*′, a substituted or unsubstituted C₃-C₆₀ carbocyclicgroup, and a substituted or unsubstituted C₁-C₆₀ heterocyclic group.

For example, L₁ may be selected from a substituted or unsubstitutedC₃-C₆₀ carbocyclic group, and a substituted or unsubstituted C₁-C₆₀heterocyclic group, but embodiments of the present disclosure are notlimited thereto.

In one embodiment, L₁, L₁₁, and L₁₂ may each independently be selectedfrom:

*—O—*′, a benzene group, a pentalene group, an indene group, anaphthalene group, an azulene group, a heptalene group, an indacenegroup, an acenaphthalene group, a fluorene group, a spiro-bifluorenegroup, a spiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group;

a benzene group, a pentalene group, an indene group, a naphthalenegroup, an azulene group, a heptalene group, an indacene group, anacenaphthalene group, a fluorene group, a spiro-bifluorene group, aspiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group, eachsubstituted with at least one selected from deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂), and

Qi and Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, and a pyridinyl group.

In one embodiment, L₁, L₁₁, and L₁₂ may each independently be selectedfrom *—O—*′ and groups represented by Formulae 3-1 to 3-29:

In Formulae 3-1 to 3-29,

Y₁ may be selected from C(Z₃)(Z₄), N(Z₅), Si(Z₆)(Z₇), O, and S,

Z₁ to Z₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, a silolyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, and a pyridinyl group,

d2 may be an integer from 0 to 2,

d3 may be an integer from 0 to 3,

d4 may be an integer from 0 to 4,

d6 may be an integer from 0 to 6,

d8 may be an integer from 0 to 8, and

* and *′ each indicate a binding site to a neighboring atom.

For example, L₁ may be a group represented by Formula 3-1.

In Formulae 1-1 to 1-2 and 2, a1 may be an integer from 1 to 5, and

a11 and a12 may each independently be an integer from 0 to 4.

In one embodiment, a1 may be 1 or 2.

In one embodiment, a11 and a12 may each independently be an integer from0 to 2.

In Formulae 1-1 to 1-2 and 2, Ar₁ and Ar₂ may each independently beselected from a substituted or unsubstituted C₃-C₆₀ carbocyclic groupand a substituted or unsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, Ar₁ and Ar₂ may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, an adamantanylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a triazinyl group, a thiophenyl group, a furanylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, a dibenzosilolyl group, a benzonaphtho silolylgroup, a dinaphtho silolyl group, a benzimidazolyl group, aphenanthrolinyl group, and an imidazopyridinyl group;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, an adamantanylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a triazinyl group, a thiophenyl group, a furanylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, a dibenzosilolyl group, a benzonaphtho silolylgroup, a dinaphtho silolyl group, a benzimidazolyl group, aphenanthrolinyl group, and an imidazopyridinyl group, each substitutedwith at least one selected from deuterium, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a triphenylenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, an adamantanyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a thiophenyl group, a furanyl group, a quinolinylgroup, an isoquinolinyl group, a benzofuranyl group, a benzothiophenylgroup, a dibenzosilolyl group, a benzonaphtho silolyl group, a dinaphthosilolyl group, a benzimidazolyl group, a phenanthrolinyl group, animidazopyridinyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and—P(═O)(Q₃₁)(Q₃₂); and

—N(Q₁)(Q₂), —B(Q₁)(Q₂), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), and

Q₁, Q₂, and Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, and a pyridinyl group.

In Formulae 1-1 to 1-2 and 2, Ar₁ and Ar₂ may each independently beselected from a substituted or unsubstituted C₃-C₆₀ carbocyclic groupand a substituted or unsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, Ar₁ and Ar₂ may each independently be selected fromgroups represented by Formulae 4-1 to 4-15:

In Formulae 4-1 to 4-15,

Y₃₁ may be selected from C(Z₃₄)(Z₃₅), N(Z₃₆), Si(Z₃₇)(Z₃₈), O, and S,

Z₃₁ to Z₃₈ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, atriazinyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₂₀ alkyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, a biphenyl group, aterphenyl group, and a phenyl group substituted with a C₁-C₂₀ alkylgroup,

e3 may be an integer from 0 to 3,

e4 may be an integer from 0 to 4,

e5 may be an integer from 0 to 5,

e6 may be an integer from 0 to 6,

e7 may be an integer from 0 to 7,

e15 may be an integer from 0 to 15, and

* indicates a binding site to a neighboring atom.

For example, in Formula 2, Ar₁ and Ar₂ may not be linked.

In Formulae 1-1 to 1-2, and 2, R₁ to R₁₄ may each independently beselected from a group represented by Formula 2, hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

at least one selected from selected from R₅ to R₈ may be a grouprepresented by Formula 2,

R₁ to R₄ may not include a carbazole group,

any two neighboring groups among R₁ to R₁₄ may optionally be linked toform substituted or unsubstituted C₃-C₆₀ carbocyclic group or C₁-C₆₀heterocyclic group.

In one embodiment, R₁ to R₁₄ may each independently be selected from:

a group represented by Formula 2, a phenyl group, a biphenyl group, aterphenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, apyrenyl group, a triphenylenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, an adamantanyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a thiophenyl group, a furanyl group, a quinolinyl group, anisoquinolinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzosilolyl group, a benzonaphtho silolyl group, a dinaphtho silolylgroup, a benzimidazolyl group, a phenanthrolinyl group, and animidazopyridinyl group;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, an adamantanylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a triazinyl group, a thiophenyl group, a furanylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, a dibenzosilolyl group, a benzonaphtho silolylgroup, a dinaphtho silolyl group, a benzimidazolyl group, aphenanthrolinyl group, and an imidazopyridinyl group, each substitutedwith at least one selected from deuterium, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a triphenylenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, an adamantanyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a thiophenyl group, a furanyl group, a quinolinylgroup, an isoquinolinyl group, a benzofuranyl group, a benzothiophenylgroup, a dibenzosilolyl group, a benzonaphtho silolyl group, a dinaphthosilolyl group, a benzimidazolyl group, a phenanthrolinyl group, animidazopyridinyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and—P(═O)(Q₃₁)(Q₃₂); and

—B(Q₁)(Q₂), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), and

Q₁, Q₂, and Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, and a pyridinyl group.

For example, in Formula 1-1, i) R₁ to R₄ and R₉ to R₁₀ may be hydrogen,ii) R₁ to R₄ may be hydrogen, and R₉ to R₁₀ may linked to form a benzenegroup.

For example, in Formula 1-2, i) R₁ to R₄ and R₉ to R₁₂ may eachindependently be hydrogen, ii) R₁ to R₄ and R₉ to R₁₀ may eachindependently be hydrogen, and R₁₁ and R₁₂ may be linked to form abenzene group, iii) R₁ to R₂ and R₉ to R₁₂ may each independently behydrogen, and R₃ and R₄ may be formed to form a benzene group or apyridine group.

For example, i) R₅ may be a group represented by Formula 2, and R₆ to R₈may each independently be hydrogen ii) R₆ may be a group represented byFormula 2, and R₅, R₇, and R₈ may each independently be hydrogen iii) R₇may be a group represented by Formula 2, and R₅, R₆, and R₈ may eachindependently be hydrogen, and iv) R₈ a group represented by Formula 2,and R₅ to R₇ may each independently be hydrogen.

At least one substituent of the substituted C₃-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₂-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, a terphenyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Qi to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with a C₁-C₆₀alkyl group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group.

In one embodiment, the condensed cyclic compound may be selected fromCompounds A1 to A119 and B1 to B119, but embodiments of the presentdisclosure are not limited thereto:

The condensed cyclic compound includes a heterohelicene moietyrepresented by Formula 1-1 or 1-2. Therethrough a π conjugation systemis long, and thermal and charge resistance thereof are excellent,thereby exhibiting a long lifespan, and since a plurality of heteroatomsare included in the heterohelicene moiety, hole transport capability canbe improved.

In addition, since the condensed cyclic compound includes thecondensation moiety, the symmetry and crystallinity of the wholemolecule are deteriorated, thereby improving the film characteristics.

Even when a condensed dibenzofuran (or dibenzothiophene, dibenzosilole)moiety is included as above, if the condensation moiety of the presentdisclosure is not included, the planarity of the whole molecule becomestoo high to improve the crystallinity, the distance between molecules isshortened, the transfer of holes is slowed, resulting in poorluminescent efficiency.

In addition, the condensed cyclic compound limits the heteroatomincluded in the heterohelicene core to O, Si, or S. Thus, as comparedwith the case of including N as the heteroatom, excellent carrierbalance can be provided, thereby improving the device efficiency.

In addition, the condensed cyclic compound essentially includes a linkerbetween a group represented by Formula 1-1 or 1-2 and an amine group. Ina case where no linker is included and thus the amine group is directlylinked to a group represented by Formula 1-1 or 1-2, the distancebetween three aryl groups linked to the nitrogen atom is excessivelyclose. Thus, the stability of molecule is deteriorated, and athree-dimensional structure capable of distorting three aryl groups istaken so as to solve a three-dimensional electronic repulsion. Thus,since HOMO orbital distribution becomes narrow, the efficiency andlifespan of the device are deteriorated.

In addition, since the condensed cyclic compound includes the aminegroup represented by Formula 2, it can be applied as a hole transportmaterial having a long lifespan due to the aryl group having strongelectron resistance, and the condensed cyclic compound limits thesubstitution position of the amine group to the terminus of theheterohelicene core. When the amine group is substituted at not theterminus of the core but the central site, the heteroatoms in theheterohelicene are directed toward the core of the whole molecule, andthe interaction between molecules becomes weak. Thus, the hole transportcapability is hardly increased, and in the HOMO orbital, the electrondistribution of the core is excessively large. Thus, the contribution tothe condensed cyclic compound of the amine group is relatively reduced.Consequently, it is difficult to exhibit characteristics arising fromthe amine group.

Furthermore, the carbazole group is not included in the terminus of thecore of the condensed cyclic compound. If the carbazole group isincluded in the condensed cyclic compound, resulting that hole transportcapability is not sufficient, and a three-dimensional structure in whichthe molecule is excessively distorted as a whole is taken. Thus, thecompound becomes unstable in a radical state, and thus the efficiencyand lifespan of the device using the compound are all deteriorated.

Therefore, an electronic device, for example, an organic light-emittingdevice, which includes the condensed cyclic compound represented byFormula 1, may have a low driving voltage, high efficiency, and a longlifespan.

A synthesis method for the condensed cyclic compound represented byFormula 1 would be apparent to those of ordinary skill in the art byreferring to the following examples.

At least one condensed cyclic compound represented by Formula 1 may beused between a pair of electrodes constituting an organic light-emittingdevice. For example, the condensed cyclic compound may be included in atleast one selected from a hole transport region and an emission layer.In one or more embodiments, the condensed cyclic compound of Formula 1may be used as a material for a capping layer located outside a pair ofelectrodes of an organic light-emitting device.

For example, the organic light-emitting device may have i) a stackedstructure including a first electrode, an organic layer, a secondelectrode, and a second capping layer which are sequentially stacked inthis stated order, ii) a stacked structure including a first cappinglayer, a first electrode, an organic layer, and a second electrode whichare sequentially stacked in this stated order, or iii) a stackedstructure including a first capping layer, a first electrode, an organiclayer, a second electrode, and a second capping layer which aresequentially stacked in this stated order, and at least one selectedfrom the first capping layer and the second capping layer may includethe condensed cyclic compound.

Accordingly, provided is an organic light-emitting device including: afirst electrode, a second electrode facing the first electrode, and anorganic layer between the first electrode and the second electrode, theorganic layer including an emission layer and at least one condensedcyclic compound represented by Formula 1.

The expression “(an organic layer) includes at least one of thecondensed cyclic compounds” used herein may include a case in which “(anorganic layer) includes identical condensed cyclic compounds representedby Formula 1” and a case in which “(an organic layer) includes two ormore different condensed cyclic compounds represented by Formula 1.”

For example, the organic layer may include, as the condensed cycliccompound, only Compound A1. In this regard, Compound A1 may exist in ahole transport layer of the organic light-emitting device. In one ormore embodiments, the organic layer may include, as the condensed cycliccompound, Compounds A1 and Compound A2. In this regard, Compound A1 andCompound A2 may exist in an identical layer (for example, Compound 1 andCompound 2 may all exist in a hole transport layer), or different layers(for example, Compound 1 may exist in an emission layer and Compound 2may exist in a hole transport layer).

According to one embodiment,

the first electrode of the organic light-emitting device may be ananode,

the second electrode of the organic light-emitting device may be acathode,

the organic layer of the organic light-emitting device may furtherinclude a hole transport region between the first electrode and theemission layer and an electron transport region between the emissionlayer and the second electrode,

the hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, a buffer layer, anemission auxiliary layer, and an electron blocking layer, and

the electron transport region may include an electron transport regionincluding at least one layer selected from a hole blocking layer, anelectron transport layer, and an electron injection layer.

In one or more embodiments, the hole transport region may include thecondensed cyclic compound represented by Formula 1.

In one or more embodiments, the hole transport region includes a holetransport layer, which includes the condensed cyclic compound.

In one embodiment, the hole transport region may include: a first holetransport layer disposed between the first electrode and the emissionlayer; and a second hole transport layer disposed between the first holetransport layer and the emission layer, and

the first hole transport layer may include the condensed cycliccompound.

In one or more embodiments, the hole transport region may include: afirst hole transport layer disposed between the first electrode and theemission layer; a second hole transport layer between the first holetransport layer and the emission layer, and

the second hole transport layer may include the condensed cycliccompound.

In one embodiment, the emission layer may include a host and a dopant,and the dopant may be a fluorescent dopant or a phosphorescent dopant.For example, the host may include an anthracene-based compound, apyrene-based compound, a fluoranthene-based compound, a chrysene-basedcompound, a dihydrobenzanthracene-based compound, a triphenylene-basedcompound, and any combination thereof.

At least one layer selected from the electron transport layer and theelectron injection layer may include an alkali metal, an alkaline earthmetal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

In one embodiment, the emission layer may be a first emission layer foremitting a first color light,

For example, the organic light-emitting device may further include i) atleast one second emission layer for emitting a second color light or ii)at least one second emission layer for emitting the second color lightand at least one third emission layer for emitting a third color light,between the first electrode and the second electrode, a maximum emissionwavelength of the first color light, a maximum emission wavelength ofthe second color light, and a maximum emission wavelength of the thirdcolor light may be identical to or different from each other.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers between the first electrode and the secondelectrode of an organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material.

[Description of FIG. 1 ]

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. The organic light-emitting device 10includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1 .

[First Electrode 110]

In FIG. 1 , a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or a plastic substrate, each having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials with a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming afirst electrode may be selected from indium tin oxide (ITO), indium zincoxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto. When the first electrode 110 is a semi-transmissive electrodeor a reflective electrode, as a material for forming the first electrode110, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), or any combination thereof may be used. However, the materialfor forming the first electrode 110 is not limited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

[Organic Layer 150]

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer, and an electrontransport region between the emission layer and the second electrode190.

[Hole Transport Region in Organic Layer 150]

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

In one embodiment, the hole transport region may include the condensedcyclic compound.

The hole transport region may further include at least one selected fromm-MTDATA, TDATA, 1-TNATA, 2-TNATA, NPB(NPD), p-NPB, TPD, Spiro-TPD,Spiro-NPB, methylated-NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), PEDOT/PSS(poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10,

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁ and R₂₀₂ may optionally be linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup, and R₂₀₃ and R₂₀₄ may optionally be linked via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one or more embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be defined the same as describedabove.

In one or more embodiments, in Formula 201, at least one selected fromR₂₀₁ to R₂₀₃ may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, in Formula 202, at least one selected fromR₂₀₁ to R₂₀₄ may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A(1) below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1 below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed above,

R₂₁₁ and R₂₁₂ may be understood by referring to the description providedherein in connection with R₂₀₃,

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one of a hole injection layerand a hole transport layer, the thickness of the hole injection layermay be in a range of about 100 Å to about 9,000 Å, and for example,about 100 Å to about 1,000 Λ, and the thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, and for example,about 100 Å to about 1,500 Å. When the thicknesses of the hole transportregion, the hole injection layer, and the hole transport layer arewithin these ranges, satisfactory hole transporting characteristics maybe obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

[p-Dopant]

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a lowest unoccupied molecularorbital (LUMO) level of −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

For example, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8, 9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221 below:

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br and a C₁-C₂₀ alkyl group substituted with —I.

[Emission Layer in Organic Layer 150]

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

In the emission layer, an amount of the dopant material may be in arange of about 0.01 parts to about 15 parts by weight based on 100 partsby weight of the host material, but embodiments of the presentdisclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

[Host in Emission Layer]

In one or more embodiments, the host may include a compound representedby Formula 301 below.[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)  <Formula 301>

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, Ar₃₀₁ in Formula 301 may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group. However, embodiments of the presentdisclosure are not limited thereto.

When xb11 in Formula 301 is two or more, two or more Ar301(s) may belinked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2:

wherein in Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene, anaphthalene, a phenanthrene, a fluoranthene, a triphenylene, a pyrene, achrysene, a pyridine, a pyrimidine, an indene, a fluorene, aspiro-bifluorene, a benzofluorene, a dibenzofluorene, an indole, acarbazole, benzocarbazole, dibenzocarbazole, a furan, a benzofuran, adibenzofuran, a naphthofuran, a benzonaphthofuran, dinaphthofuran, athiophene, a benzothiophene, a dibenzothiophene, a naphthothiophene, abenzonaphthothiophene, and a dinaphthothiophene,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ may each independently be defined thesame as described above,

L₃₀₂ to L₃₀₄ may each independently be defined the same as describedabove L₃₀₁,

xb2 to xb4 may each independently be defined the same as described abovexb1, and

R₃₀₂ to R₃₀₄ may each independently be defined the same as describedabove R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be defined the same as describedabove.

In one embodiment, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ and Q₃₃ may each independently be defined the same as describedabove.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a Be complex (forexample, Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), a4,4′-bis(N-carbazolyl)-1, 1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:M(L₄₀₁)_(xc1)(L₄₀₂)_(xc2)  <Formula 401>

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1 is two or more, two or more L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein, when xc2 is two or more, two or more L₄₀₂(s) may be identicalto or different from each other,

X_(4o01) to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be selected from a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*, *—C(Q₄₁₁)=*′, or *=C=*′,wherein Q₄₁₁ and Q₄₁₂ may each independently be hydrogen, deuterium, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃),—N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and—P(═O)(Q₄₀₁)(Q₄₀₂), wherein Q₄₀₁ to Q₄₀₃ may each independently beselected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ arylgroup, and a C₁-C₂₀ heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

in Formula 402, * and *′ each indicate a binding site to M in Formula401.

In one embodiment, A₄₀₁ and A₄₀₂ in Formula 402 may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may each be nitrogen at thesame time.

In one or more embodiments, R₄₀₂ and R₄₀₂ in Formula 401 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a phenyl group, a naphthyl group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, and a norbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but are not limited thereto.

In one or more embodiments, when xc1 in Formula 401 is two or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, whichis a linking group, or two A₄₀₂(s) in two or more L₄₀₁(s) may optionallybe linked via X₄₀₈, which is a linking group (see Compounds PD1 to PD4and PD7). X₄₀₇ and X₄₀₈ may each independently be a single bond, *—O—*′,*—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)-*′, *—C(Q₄₁₃)(Q₄₁₄)-*′, or*—C(Q₄₁₃)=C(Q₄₁₄)-*′ (wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from halogen, diketone (forexample, acetylacetonate), carboxylic acid (for example, picolinate),—C(═O), isonitrile, —CN, and a phosphorus-containing material (forexample, phosphine, or phosphite), but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

[Fluorescent Dopant in Emission Layer]

The fluorescent dopant may include an arylamine compound or astyrylamine compound.

The fluorescent dopant may include a compound represented by Formula 501below.

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L_(50l) to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer of 0 to 3;

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,

xd4 may be an integer of 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each be selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and anaphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto.

[Electron Transport Region in Organic Layer 150]

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one rr electron-depletednitrogen-containing ring.

The “π electron-depleted nitrogen-containing ring” indicates a C₁-C₆₀heterocyclic group having at least one *—N═*′ moiety as a ring-formingmoiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 5-membered to 7-membered heteromonocyclic group having at least one*—N═*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N═*′ moiety are condensed with each other, or iii) aheteropolycyclic group in which at least one of 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N═*′ moiety, iscondensed with at least one C₅-C₆₀ carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring include animidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, anisoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, indazole,a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine,a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, aphenanthridine, an acridine, a phenanthroline, a phenazine, abenzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, atriazole, a tetrazole, an oxadiazole, a triazine, thiadiazole, animidazopyridine, an imidazopyrimidine, and an azacarbazole, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe11)-R₆₀₁]_(xe21).  <Formula 601>

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 and/orat least one of R₆₀₁(s) in the number of xe21 may include the πelectron-depleted nitrogen-containing ring.

In one embodiment, ring Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is two or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, a compound represented by Formula 601 may berepresented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be the same as described inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁,

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group, but are not limited thereto,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, R₆₀₁ and R₆₁₁ to R₆₁₃ in Formula 601 and601-1 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ may be the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ.

The thickness of the buffer layer, the hole blocking layer, or theelectron controlling layer may each independently be in a range of about20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When thethicknesses of the buffer layer, the hole blocking layer, and theelectron control layer are within these ranges, the electron blockinglayer may have excellent electron blocking characteristics or electroncontrol characteristics without a substantial increase in drivingvoltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have satisfactoryelectron transport characteristics without a substantial increase indriving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxydiphenylthiadiazol, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2.

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, KI, or RbI. In one embodiment, the alkali metalcompound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), orBa_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, Ybl₃, Scl₃, and Tbl₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazol,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof, as described above. In one or moreembodiments, the electron injection layer may further include an organicmaterial. When the electron injection layer further includes an organicmaterial, an alkali metal, an alkaline earth metal, a rare earth metal,an alkali metal compound, an alkaline earth-metal compound, a rare earthmetal compound, an alkali metal complex, an alkaline earth-metalcomplex, a rare earth metal complex, or any combinations thereof may behomogeneously or non-homogeneously dispersed in a matrix including theorganic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

[Second Electrode 190]

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode that is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be a material having a low work function,and such a material may be metal, alloy, an electrically conductivecompound, or a combination thereof.

The second electrode 190 may include at least one selected from lithium(Li), silver (Si), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

[Description of FIGS. 2 to 4 ]

An organic light-emitting device 20 of FIG. 2 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, and a secondelectrode 190 which are sequentially stacked in this stated order. Anorganic light-emitting device 30 of FIG. 3 includes a first electrode110, an organic layer 150, a second electrode 190, and a second cappinglayer 220 which are sequentially stacked in this stated order. Anorganic light-emitting device 40 of FIG. 4 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, a secondelectrode 190, and a second capping layer 220.

Regarding FIGS. 2 to 4 , the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1 .

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer 210 toward theoutside. In the organic layer 150 of each of the organic light-emittingdevices 30 and 40, light generated in an emission layer may pass throughthe second electrode 190, which is a semi-transmissive electrode or atransmissive electrode, and the second capping layer 220 toward theoutside.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescent efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives, anaphthalocyanine derivatives, alkali metal complexes, and alkalineearth-based complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selectedfrom the first capping layer 210 and the second capping layer 220 mayeach independently include an amine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto.

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1 to 4 . However,embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to 200° C., depending on a material to be included in alayer and the structure of each layer to be formed.

[General Definition of Substituents]

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched saturated aliphatic hydrocarbon monovalent group having 1 to 60carbon atoms, and non-limiting examples thereof include a methyl group,an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup formed by substituting at least one carbon-carbon double bond inthe middle or at the terminus of the C₂-C₆₀ alkyl group, andnon-limiting examples thereof include an ethenyl group, a propenylgroup, and a butenyl group. The term “C₂-C₆₀ alkenylene group” as usedherein refers to a divalent group having the same structure as theC₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup formed by substituting at least one carbon-carbon triple bond inthe middle or at the terminus of the C₂-C₆₀ alkyl group, andnon-limiting examples thereof include an ethynyl group, and a propynylgroup. The term “C₂-C₆₀ alkynylene group” as used herein refers to adivalent group having the same structure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and non-limiting examples thereof include a methoxy group, an ethoxygroup, and an isopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁ heterocycloalkyl group” as used herein refers to amonovalent saturated monocyclic group having at least one heteroatomselected from N, O, Si, P, and S as a ring-forming atom and 1 to 10carbon atoms, and non-limiting examples thereof include a1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, atetrahydrothiophenyl group. The term “C₁-C₁ heterocycloalkylene group”as used herein refers to a divalent group having the same structure asthe C₁-C₁ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and non-limiting examples thereof include a cyclopentenyl group, acyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₁-C₁ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused toeach other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, inaddition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group”as used herein refers to a divalent group having a heterocyclic aromaticsystem that has at least one heteroatom selected from N, O, Si, P, and Sas a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be fused to each other.

The term “C₆-C₆₀ aryloxy group” as used herein refers to —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group used hereinindicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. A detailed example of the monovalent non-aromatic condensedpolycyclic group is a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other, at leastone heteroatom selected from N, O, Si, P, and S, other than carbonatoms, as a ring-forming atom, and no aromaticity in its entiremolecular structure. An example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group” as used herein refers toa divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which aring-forming atom is a carbon atom only. The C₅-C₆₀ carbocyclic groupmay be an aromatic carbocyclic group or a non-aromatic carbocyclicgroup. The C₅-C₆₀ carbocyclic group may be a ring, such as benzene, amonovalent group, such as a phenyl group, or a divalent group, such as aphenylene group. In one or more embodiments, depending on the number ofsubstituents connected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group” as used herein refers to a grouphaving the same structure as the C₁-C₆₀ carbocyclic group, except thatas a ring-forming atom, at least one heteroatom selected from N, O, Si,P, and S is used in addition to carbon (the number of carbon atoms maybe in a range of 1 to 60).

At least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph”, as used herein, may refer to a phenyl group; the term“Me”, as used herein, may refer to a methyl group; the term “Et”, asused herein, may refer to an ethyl group; the terms “ter-Bu” or “But”,as used herein, may refer to a tert-butyl group; and the term “OMe” asused herein may refer to a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′ used herein, unless defined otherwise, each refer to a bindingsite to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described indetail with reference to Synthesis Examples and Examples. The wording “Bwas used instead of A” used in describing Synthesis Examples andExamples refers to that an identical molar equivalent of B was used inplace of A.

EXAMPLES Synthesis Example 1: Synthesis of Compound A5

(Synthesis of Intermediate IM-1)

In an Ar atmosphere, 20.00 g (73.56 mmol) of2,3-dibromo-1,4-difluorobenzene, 12.30 g (1.1 equiv, 80.9 mmol) of2-methoxyphenylboronic acid, 80.92 g (3 equiv, 220.7 mmol) of K₂CO₃,4.25 g (0.05 equiv, 3.7 mmol) of Pd(PPh₃)₄, and 515 mL of a mixedsolution of toluene/EtOH/H₂O (4/2/1) were sequentially added to a1,000-mL three-neck flask, and heated and stirred at a temperature of80° C. for 5 hours. After cooling to room temperature, the reactionsolution was extracted therefrom by using toluene. A water layer wasremoved therefrom, and an organic layer was cleaned by using saturatedsaline and dried by using MgSO₄. MgSO₄ was filtered and separated andthe organic layer was concentrated. A crude product obtained therefromwas purified by silica gel column chromatography (mixed solvent ofhexane and toluene was used in a development layer) to obtainIntermediate IM-1 (16.94 g, yield of 77%).

Intermediate IM-1 was identified by observing the mass number m/z=299 asthe molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-2)

In an Ar atmosphere, 15.00 g (50.1 mmol) of Intermediate IM-1, 10.28 g(1.1 equiv, 55.2 mmol) of 2-chloro-6-methoxyphenylboronic acid, 20.79 g(3 equiv, 150.4 mmol) of K₂CO₃, 2.90 g (0.05 equiv, 2.5 mmol) ofPd(PPh₃)₄, and 350 mL of a mixed solution of toluene/EtOH/H₂O (4/2/1)were sequentially added to a 500-mL three-neck flask, and heated andstirred at a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-2 (14.66 g, yield of 81%).

Intermediate IM-2 was identified by observing the mass number m/z=360 asthe molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-3)

In an Ar atmosphere, 13.00 g (36.0 mmol) of Intermediate IM-2, 120 mL ofCH₂Cl₂, and 216 mL (6 equiv, 216.2 mmol) of CH₂Cl₂ solution of 1 M BBr₃were sequentially added to a 500-mL three-neck flask, and heated andstirred at room temperature for 24 hours. The reaction solution wasneutralized by using saturated NaHCO₃ aqueous solution, and an organiclayer was extracted therefrom by using CH₂Cl₂ and cleaned by usingsaturated saline. A crude product obtained therefrom was purified bysilica gel column chromatography (mixed solvent of hexane and toluenewas used in a development layer) to obtain Intermediate IM-3 (10.07 g,yield of 84%).

Intermediate IM-3 was identified by observing the mass number m/z=332 asthe molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-4)

In an Ar atmosphere, 10.00 g (30.0 mmol) of Intermediate IM-3, 150 mL ofNMP, and 16.62 g (4 equiv, 120.2 mmol) of K₂CO₃ were sequentially addedto a 300-mL three-neck flask, and heated and stirred at a temperature of180° C. for 5 hours. After the reaction solution was cooled to roomtemperature, H₂O was added to the reaction solution and an organic layerwas extracted therefrom by using toluene. The organic layer was cleanedby using saturated saline and dried by using MgSO₄. MgSO₄ was filteredand separated and the organic layer was concentrated. A crude productobtained therefrom was purified by silica gel column chromatography(mixed solvent of hexane and toluene was used in a development layer) toobtain Intermediate IM-4 (6.07 g, yield of 69%).

Intermediate IM-4 was identified by observing the mass number m/z=292 asthe molecular ion peak through FAB-MS.

(Synthesis of Compound A5)

In an Ar atmosphere, 5.00 g (17.08 mmol) of Intermediate IM-4, 9.84 g(1.1 equiv, 18.8 mmol) of N,N-Di(4-biphenylyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,7.08 g (3 equiv, 51.2 mmol) of K₂CO₃, 0.98 g (0.05 equiv, 0.9 mmol) ofPd(PPh₃)₄, and 120 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. The reaction mixture was cooledto room temperature, and the reaction solution was extracted therefromby using toluene. A water layer was removed therefrom, and an organiclayer was cleaned by using saturated saline and dried by using MgSO₄.MgSO₄ was filtered and separated and the organic layer was concentrated.A crude product obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound A5 (9.51 g, yield of 87%) that wasa white solid.

Compound A5 was identified by observing the mass number m/z=653 as themolecular ion peak through FAB-MS.

Synthesis Example 2: Synthesis of Compound A21

In an Ar atmosphere, 5.00 g (73.56 mmol) of Intermediate IM-4, 9.84 g(1.1 equiv, 18.8 mmol) ofN,N-di(4-biphenylyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,7.08 g (3 equiv, 51.2 mmol) of K₂CO₃, 0.98 g (0.05 equiv, 0.9 mmol) ofPd(PPh₃)₄, and 120 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound A21 (9.18 g, yield of 84%) thatwas a white solid.

Compound A21 was identified by observing the mass number m/z=653 as themolecular ion peak through FAB-MS.

Synthesis Example 3: Synthesis of Compound A73

(Synthesis of Intermediate IM-5)

In an Ar atmosphere, 20.00 g (126.07 mmol) of 2-chlorophenyl methylsulfide and 420 mL (0.3 M) of THF were stirred at a temperature of −78°C. in a 1,000-mL three-neck flask, and 86.7 mL (1.1 equiv) of 1.6 mol/Ln-BuLi/n-hexane solution was added dropwise thereto. After the reactionmixture was stirred at the same temperature for 1 hour, 65.50 g (5equiv, 630.4 mmol) of trimethyl borate was added dropwise thereto andstirred at the same temperature for 2 hours, and the reaction mixturewas heated to room temperature and stirred again for 2 hours. 250 mL of1 N HCl was added thereto, and the reaction solution was extractedtherefrom by using toluene. A water layer was removed therefrom, and anorganic layer was sequentially cleaned by aqueous solution of sodiumhydrogen carbonate and saturated saline and dried by using MgSO₄. MgSO₄was filtered and separated and the organic layer was concentrated. Acrude product obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-5 (18.38 g, yield of 72%).

Intermediate IM-5 was identified by observing the mass number m/z=202 asthe molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-6)

In an Ar atmosphere, 15.00 g (74.1 mmol) of Intermediate IM-5, 20.14 g(1.1 equiv, 81.5 mmol) of 1-bromo-dibenzofuran, 30.72 g (3 equiv, 222.3mmol) of K₂CO₃, 4.28 g (0.05 equiv, 3.7 mmol) of Pd(PPh₃)₄, and 518 mLof mixed solution of toluene/EtOH/H₂O (4/2/1) were sequentially added toa 1,000-mL three-neck flask, and heated and stirred at a temperature of80° C. for 5 hours. After cooling to room temperature, the reactionsolution was extracted therefrom by using toluene. A water layer wasremoved therefrom, and an organic layer was cleaned by using saturatedsaline and dried by using MgSO₄. MgSO₄ was filtered and separated andthe organic layer was concentrated. A crude product obtained therefromwas purified by silica gel column chromatography (mixed solvent ofhexane and toluene was used in a development layer) to obtainIntermediate IM-6 (19.01 g, yield of 79%).

Intermediate IM-6 was identified by observing the mass number m/z=324 asthe molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-7)

In an Ar atmosphere, 15.00 g (46.2 mmol) of Intermediate IM-6 and 184 mL(0.25 M) of AcOH were added to a 500-mL three-neck flask and stirred ata temperature of 0° C., and 184 mL of AcOH solution containing 35%hydrogen peroxide (4.62 g) was added dropwise thereto. The reactionsolution was heated and stirred at the same temperature for 2 hours, andAcOH of the reaction solution was distilled under reduced pressure. Acrude product obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-7 (14.01 g, yield of 89%).

Intermediate IM-7 was identified by observing the mass number m/z=340 asthe molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-8)

In an Ar atmosphere, 10.00 g (29.3 mmol) of Intermediate IM-7 and 44.0 g(10 equiv, 293.4 mmol) of trifluoromethanesulfonic acid weresequentially added to a 300-mL three-neck flask, and stirred at roomtemperature for 24 hours. The reaction solution was slowly added to 98mL of mixed solution of H₂O/pyridine (8:1) and heated and stirred for 1hour under reflux. After cooling to room temperature, the reactionsolution was extracted therefrom by using toluene. A water layer wasremoved therefrom, and an organic layer was cleaned by using saturatedsaline and dried by using MgSO₄. MgSO₄ was filtered and separated andthe organic layer was concentrated. A crude product obtained therefromwas purified by silica gel column chromatography (mixed solvent ofhexane and toluene was used in a development layer) to obtainIntermediate IM-8 (7.25 g, yield of 80%).

Intermediate IM-8 was identified by observing the mass number m/z=308 asthe molecular ion peak through FAB-MS.

(Synthesis of Compound A73)

In an Ar atmosphere, 5.00 g (16.2 mmol) of Intermediate IM-8, 9.32 g(1.1 equiv, 17.8 mmol) ofN-phenyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-(1,1′:4′,1″-terphenyl)-4-amine,6.71 g (3 equiv, 48.6 mmol) of K₂CO₃, 0.94 g (0.05 equiv, 0.8 mmol) ofPd(PPh₃)₄, and 113 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound A73 (9.33 g, yield of 86%) thatwas a white solid.

Compound A73 was identified by observing the mass number m/z=669 as themolecular ion peak through FAB-MS.

Synthesis Example 4: Synthesis of Compound A100

(Synthesis of Intermediate IM-9)

In an Ar atmosphere, 10.00 g (34.4 mmol) ofbenzo[1,2-b:4,3-b′]bis[1]benzothiophene, 172 mL of CH₂Cl₂, and 7.35 g(1.2 equiv, 41.3 mmol) of N-bromosuccinimide were sequentially added toa 300-mL three-neck flask, and stirred at room temperature for 4 hours.H₂O was added to the reaction solution, and the reaction solution wasextracted therefrom. A water layer was removed therefrom, and an organiclayer was cleaned by using saturated saline and dried by using MgSO₄.MgSO₄ was filtered and separated and the organic layer was concentrated.A crude product obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-9 (8.39 g, yield of 66%).

Intermediate IM-9 was identified by observing the mass number m/z=369 asthe molecular ion peak through FAB-MS.

(Synthesis of Compound A100)

In an Ar atmosphere, 5.00 g (13.5 mmol) of Intermediate IM-9, 9.11 g(1.1 equiv, 14.9 mmol) ofN,9,9-triphenyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-fluoren-2-amine,5.61 g (3 equiv, 40.6 mmol) of K₂CO₃, 0.78 g (0.05 equiv, 0.7 mmol) ofPd(PPh₃)₄, and 95 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 300-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound A100 (8.70 g, yield of 83%) thatwas a white solid.

Compound A100 was identified by observing the mass number m/z=774 as themolecular ion peak through FAB-MS.

Synthesis Example 5: Synthesis of Compound B5

(Synthesis of Intermediate IM-10)

In an Ar atmosphere, 25.00 g (78.63 mmol) of1,8-dibromo-2,7-dihydroxynaphthalene, 12.10 g (1.1 equiv, 86.49 mmol) of2-fluorophenylboronic acid, 32.60 g (3 equiv, 235.9 mmol) of K₂CO₃, 4.54g (0.05 equiv, 3.9 mmol) of Pd(PPh₃)₄, and 550 mL of mixed solution oftoluene/EtOH/H₂O (4/2/1) were sequentially added to a 1,000-mL flask,and heated and stirred at a temperature of 80° C. for 5 hours. Aftercooling to room temperature, the reaction solution was extractedtherefrom by using toluene. A water layer was removed therefrom, and anorganic layer was cleaned by using saturated saline and dried by usingMgSO₄. MgSO₄ was filtered and separated and the organic layer wasconcentrated. A crude product obtained therefrom was purified by silicagel column chromatography (mixed solvent of hexane and toluene was usedin a development layer) to obtain Intermediate IM-10 (18.60 g, yield of71%).

Intermediate IM-10 was identified by observing the mass number m/z=333as the molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-11)

In an Ar atmosphere, 12.00 g (36.02 mmol) of Intermediate IM-10, 6.91 g(1.1 equiv, 39.6 mmol) of 2-chloro-6-fluorophenylboronic acid, 14.93 g(3 equiv, 108.06 mmol) of K₂CO₃, 2.08 g (0.05 equiv, 1.8 mmol) ofPd(PPh₃)₄, and 252 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-11 (11.30 g, yield of 82%).

Intermediate IM-11 was identified by observing the mass number m/z=382as the molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-12)

In an Ar atmosphere, 10.00 g (26.1 mmol) of Intermediate IM-11, 130 mLof NMP, and 14.44 g (4 equiv, 104.5 mmol) of K₂CO₃ were sequentiallyadded to a 300-mL three-neck flask, and heated and stirred at atemperature of 180° C. for 5 hours. After cooling to room temperature,H₂O was added to the reaction solution, and the reaction solution wasextracted therefrom. A water layer was removed therefrom, and an organiclayer was cleaned by using saturated saline and dried by using MgSO₄.MgSO₄ was filtered and separated and the organic layer was concentrated.A crude product obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-12 (7.79 g, yield of 87%).

Intermediate IM-12 was identified by observing the mass number m/z=342as the molecular ion peak through FAB-MS.

(Synthesis of Compound B5)

In an Ar atmosphere, 5.00 g (14.6 mmol) of Intermediate IM-12, 8.66 g(1.1 equiv, 16.0 mmol) of N,N-Di(4-biphenylyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,6.05 g (3 equiv, 43.8 mmol) of K₂CO₃, 0.84 g (0.05 equiv, 0.7 mmol) ofPd(PPh₃)₄, and 102 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially mixed to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound B5 (9.03 g, yield of 88%).

Compound B5 was identified by observing the mass number m/z=703 as themolecular ion peak through FAB-MS.

Synthesis Example 6: Synthesis of Compound B14

(Synthesis of Compound B14)

In an Ar atmosphere, 5.00 g (14.6 mmol) of Intermediate IM-12, 8.98 g(1.1 equiv, 16.0 mmol) ofN-(dibenzo[b,d]thiophen-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]thiophen-4-amine, 6.05 g (3 equiv, 43.8 mmol) of K₂CO₃, 0.84 g (0.05equiv, 0.7 mmol) of Pd(PPh₃)₄, and 102 mL of mixed solution oftoluene/EtOH/H₂O (4/2/1) were sequentially added to a 500-mL three-neckflask, and heated and stirred at a temperature of 80° C. for 5 hours.After cooling to room temperature, the reaction solution was extractedtherefrom by using toluene. A water layer was removed therefrom, and anorganic layer was cleaned by using saturated saline and dried by usingMgSO₄. MgSO₄ was filtered and separated and the organic layer wasconcentrated. A crude product obtained therefrom was purified by silicagel column chromatography (mixed solvent of hexane and toluene was usedin a development layer) to obtain Compound B14 (8.08 g, yield of 79%)that was a white solid.

Compound B14 was identified by observing the mass number m/z=763 as themolecular ion peak through FAB-MS.

Synthesis Example 7: Synthesis of Compound B35

(Synthesis of Intermediate IM-13)

In an Ar atmosphere, 12.00 g (36.02 mmol) of Intermediate IM-10, 6.91 g(1.1 equiv, 39.6 mmol) of 3-chloro-6-fluorophenylboronic acid, 14.93 g(3 equiv, 108.06 mmol) of K₂CO₃, 2.08 g (0.05 equiv, 1.8 mmol) ofPd(PPh₃)₄, and 252 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-13 (10.62 g, yield of 77%).

Compound B13 was identified by observing the mass number m/z=382 as themolecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-14)

In an Ar atmosphere, 10.00 g (26.1 mmol) of Intermediate IM-13, 130 mLof NMP, and 14.44 g (4 equiv, 104.5 mmol) of K₂CO₃ were sequentiallyadded to a 300-mL three-neck flask, and heated and stirred at atemperature of 180° C. for 5 hours. After cooling to room temperature,H₂O was added to the reaction solution, and the reaction solution wasextracted therefrom. An organic layer was cleaned by using saturatedsaline and dried by using MgSO₄. MgSO₄ was filtered and separated andthe organic layer was concentrated.

A crude product obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-14 (7.26 g, yield of 81%).

Intermediate IM-14 was identified by observing the mass number m/z=342as the molecular ion peak through FAB-MS.

(Synthesis of Compound B35)

In an Ar atmosphere, 5.00 g (14.6 mmol) of Intermediate IM-12, 9.68 g(1.1 equiv, 16.0 mmol) ofN-[4-(naphthalen-1-yl)phenyl[-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran-3-amine,6.05 g (3 equiv, 43.8 mmol) of K₂CO₃, 0.84 g (0.05 equiv, 0.7 mmol) ofPd(PPh₃)₄, and 500 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound B35 (8.06 g, yield of 72%) thatwas a white solid.

Compound B35 was identified by observing the mass number m/z=767 as themolecular ion peak through FAB-MS.

Synthesis Example 8: Synthesis of Compound B41

(Synthesis of Intermediate IM-15)

In an Ar atmosphere, 12.00 g (36.02 mmol) of Intermediate IM-10, 6.91 g(1.1 equiv, 39.6 mmol) of 4-chloro-2-fluorophenylboronic acid, 14.93 g(3 eqiv, 108.06 mmol) of K₂CO₃, 2.08 g (0.05 equiv, 1.8 mmol) ofPd(PPh₃)₄, and 252 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially mixed to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Intermediate IM-15 (11.03 g, yield of 80%).

Intermediate IM-15 was identified by observing the mass number m/z=382as the molecular ion peak through FAB-MS.

(Synthesis of Intermediate IM-16)

In an Ar atmosphere, 10.00 g (26.1 mmol) of IM-15, 130 mL of NMP, and14.44 g (4 equiv, 104.5 mmol) of K₂CO₃ were sequentially added to a300-mL three-neck flask, and heated and stirred at a temperature of 180°C. for 5 hours. After cooling to room temperature, H₂O was added to thereaction solution, and the reaction solution was extracted therefrom. Anorganic layer was cleaned by using saturated saline and dried by usingMgSO₄. MgSO₄ was filtered and separated and the organic layer wasconcentrated. A crude product obtained therefrom was purified by silicagel column chromatography (mixed solvent of hexane and toluene was usedin a development layer) to obtain Intermediate IM-16 (7.07 g, yield of79%).

Intermediate IM-16 was identified by observing the mass number m/z=342as the molecular ion peak through FAB-MS.

(Synthesis of Compound B41)

In an Ar atmosphere, 5.00 g (14.6 mmol) of Intermediate IM-16, 8.24 g(1.1 equiv, 16.0 mmol) ofN-[(1,1′-biphenyl)-4-yl]-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]naphthalen-1-amine,6.05 g (3 equiv, 43.8 mmol) of K₂CO₃, 0.84 g (0.05 equiv, 0.7 mmol) ofPd(PPh₃)₄, and 102 mL of mixed solution of toluene/EtOH/H₂O (4/2/1) weresequentially added to a 500-mL three-neck flask, and heated and stirredat a temperature of 80° C. for 5 hours. After cooling to roomtemperature, the reaction solution was extracted therefrom by usingtoluene. A water layer was removed therefrom, and an organic layer wascleaned by using saturated saline and dried by using MgSO₄. MgSO₄ wasfiltered and separated and the organic layer was concentrated. A crudeproduct obtained therefrom was purified by silica gel columnchromatography (mixed solvent of hexane and toluene was used in adevelopment layer) to obtain Compound B41 (8.21 g, yield of 83%) thatwas a white solid.

Compound B41 was identified by observing the mass number m/z=677 as themolecular ion peak through FAB-MS.

Synthesis methods of compounds other than Compounds synthesizedaccording to Synthesis Examples may also be easily recognized by thoseof ordinary skill in the art by referring to the synthesis mechanismsand source materials described above.

Example 1

As an anode, a Corning 15 Ω/cm² (1,500 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and purewater each for 5 minutes, and then cleaned by exposure to ultravioletrays and ozone for 30 minutes. Then, the ITO glass substrate wasprovided to a vacuum deposition apparatus.

1-TNATA as a known material for a hole injection layer wasvacuum-deposited on the ITO glass substrate to a thickness of 600 Å, andCompound A5 as a hole transport compound was vacuum-deposited to athickness of 300 Å, thereby forming a hole transport layer.

9,10-di(naphthalen-2-yl)anthracene (ADN) as a known blue fluorescenthost and 2,5,8,11-tetra-t-butylperylene (TBPe) as a known bluefluorescent dopant were co-deposited on the hole transport layer at aweight ratio of 97:3 to form an emission layer having a thickness of 250Å.

Alq₃ was deposited on the emission layer to form an electron transportlayer having a thickness of 250 Å, LiF, which is an alkali metal halide,was deposited on the electron transport layer to form an electroninjection layer having a thickness of 10 Å, Al was vacuum-deposited toform a cathode electrode having a thickness of 1,000 Å to form a LiF/Alelectrode, thereby completing the manufacture of an organiclight-emitting device.

Examples 2 to 8

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that Compounds shown in Table 1 were each usedinstead of Compound A5 in forming a hole transport layer.

Comparative Examples 1 to 6

Organic light-emitting devices were manufactured in the same manner asin Comparative Example 1, except that Compounds R₁ to R₆ were each usedinstead of Compound A5 in forming a hole transport layer.

Evaluation Example 1

The current density, driving voltage, luminescent efficiency, and halflifespan of the organic light-emitting devices manufactured according toExamples 1 to 8 and Comparative Examples 1 to 6 were measured at darkroom by using Source Meter (manufactured by Keithley Instrument 2400series), a chrominance luminance meter CS-200 (manufactured by KonicaMinolta), and measurement program LabVIEW 8.2, and results thereof areshown in Table 1. The half lifespan is a luminance half time fromluminance 1000 cd/m².

TABLE 1 Hole Driving Current Half transport voltage density Efficiencylifespan material (V) (mA/cm²) (cd/A) (LT50(h)) Example Compound 5.7 107.9 2050 1 A5 Example Compound 5.8 10 8.1 2000 2 A21 Example Compound5.6 10 7.6 2150 3 A73 Example Compound 5.7 10 7.7 2200 4 A100 ExampleCompound 5.6 10 8.2 2100 5 B5 Example Compound 5.8 10 8.3 2050 6 B14Example Compound 5.8 10 8.0 2150 7 B35 Example Compound 5.8 10 8.0 21008 B41 Comparative Compound 6.0 10 5.6 1400 Example R1 1 ComparativeCompound 6.0 10 6.0 1500 Example R2 2 Comparative Compound 5.9 10 6.01750 Example R3 3 Comparative Compound 6.0 10 6.3 1700 Example R4 4Comparative Compound 6.0 10 5.9 1750 Example R5 5 Comparative Compound6.4 10 5.7 1500 Example R6 6

Referring to Table 1, it is confirmed that the organic light-emittingdevices of Examples 1 to 8 have a low driving voltage and highefficiency, as compared with the organic light-emitting devices ofComparative Examples 1 to 6. In addition, it is confirmed that theorganic light-emitting devices of Examples 1 to 8 have a long lifespan,as compared with the organic light-emitting devices of ComparativeExamples 1 to 6.

The organic light-emitting device including the condensed cycliccompound may have a low driving voltage, high efficiency, and a longlifespan.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope as defined by the following claims.

What is claimed is:
 1. An organic light-emitting device comprising: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode andcomprising an emission layer, wherein the organic layer comprises atleast one of a condensed cyclic compound represented by Formula 1-1 or1-2:

wherein, in Formulae 1-1 and 1-2, X₁ and X₂ are each independently O, S,and Si(R₁₃)(R₁₄), and at least one selected from X₁ and X₂ isSi(R₁₃)(R₁₄), wherein, in Formula 2, L₁, L₁₁, and L₁₂ are eachindependently selected from *—O—*′, a substituted or unsubstitutedC₃-C₆₀ carbocyclic group, and a substituted or unsubstituted C₁-C₆₀heterocyclic group, a1 is an integer from 1 to 5, a11 and a12 are eachindependently an integer from 0 to 4, Ar₁ and Ar₂ are each independentlyselected from a substituted or unsubstituted C₃-C₆₀ carbocyclic groupand a substituted or unsubstituted C₁-C₆₀ heterocyclic group, wherein,in Formulae 1-1 and 1-2, R₅ to R₁₄ are each independently selected froma group represented by Formula 2, hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂),—S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), at least one selected from R₅ to R₈ isa group represented by Formula 2, R₁ to R₄ are each independentlyselected from a group represented by hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), and —B(Q₁)(Q₂), R₁ to R₄ do not include a carbazolegroup, any two neighboring groups among R₁ to R₁₄ are optionally linkedto form a substituted or unsubstituted C₃-C₆₀ carbocyclic group or aC₁-C₆₀ heterocyclic group, at least one substituent of the substitutedC₃-C₆₀ carbocyclic group, the substituted C₁-C₆₀ heterocyclic group, thesubstituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group,the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxygroup, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₂-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group is selectedfrom: deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, and a terphenylgroup; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, a terphenyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂), Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ areeach independently selected from hydrogen, deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryl group substituted with a C₁-C₆₀ alkyl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and * and *′ each indicate a binding siteto a neighboring atom.
 2. The organic light-emitting device of claim 1,wherein, the first electrode is an anode, the second electrode is acathode, the organic layer comprises a hole transport region between thefirst electrode and the emission layer and an electron transport regionbetween the emission layer and the second electrode, the hole transportregion comprises a hole injection layer, a hole transport layer, anemission auxiliary layer, an electron blocking layer, or any combinationthereof, and the electron transport region comprises a buffer layer, ahole blocking layer, an electron control layer, an electron transportlayer, an electron injection layer, or any combination thereof.
 3. Theorganic light-emitting device of claim 2, wherein, the hole transportregion comprises the condensed cyclic compound.
 4. The organiclight-emitting device of claim 2, wherein, the hole transport regioncomprises the hole transport layer, and the hole transport layercomprises the condensed cyclic compound.
 5. The organic light-emittingdevice of claim 4, wherein, the hole transport region comprises theemission auxiliary layer, and the emission auxiliary layer comprises thecondensed cyclic compound.
 6. The organic light-emitting device of claim1, wherein, the emission layer comprises a host and a dopant.
 7. Theorganic light-emitting device of claim 6, wherein, the host comprises ananthracene-based compound, a pyrene-based compound, a fluoranthene-basedcompound, a chrysene-based compound, a dihydrobenzanthracene-basedcompound, a triphenylene-based compound, or any combination thereof. 8.The organic light-emitting device of claim 1, wherein, the emissionlayer is a first emission layer for emitting a first color light, theorganic light-emitting device further comprises i) at least one secondemission layer for emitting a second color light or ii) at least onesecond emission layer for emitting the second color light and at leastone third emission layer for emitting a third color light, between thefirst electrode and the second electrode, a maximum emission wavelengthof the first color light, a maximum emission wavelength of the secondcolor light, and a maximum emission wavelength of the third color lightare identical to or different from each other, and the first color lightand the second color light are emitted in the form of a mixed light, orthe first color light, the second color light, and the third color lightare emitted in the form of the mixed light.
 9. A condensed cycliccompound represented by Formula 1-1 or 1-2:

wherein, in Formulae 1-1 and 1-2, X₁ and X₂ are each independently O, S,and Si(R₁₃)(R₁₄), and at least one selected from X₁ and X₂ isSi(R₁₃)(R₁₄), wherein, in Formula 2, L₁, L₁₁, and L₁₂ are eachindependently selected from *—O—*′, a substituted or unsubstitutedC₃-C₆₀ carbocyclic group, and a substituted or unsubstituted C₁-C₆₀heterocyclic group, a1 is an integer from 1 to 5, a11 and a12 are eachindependently an integer from 0 to 4, Ar₁ and Ar₂ are each independentlyselected from a substituted or unsubstituted C₃-C₆₀ carbocyclic groupand a substituted or unsubstituted C₁-C₆₀ heterocyclic group, wherein,in Formulae 1-1 and 1-2, R₅ to R₁₄ are each independently selected froma group represented by Formula 2, hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂),—S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), at least one selected from R₅ to R₈ isa group represented by Formula 2, R₁ to R₄ are each independentlyselected from a group represented by hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), and —B(Q₁)(Q₂), R₁ to R₄ do not include a carbazolegroup, any two neighboring groups among R₁ to R₁₄ are optionally linkedto form a substituted or unsubstituted C₃-C₆₀ carbocyclic group or aC₁-C₆₀ heterocyclic group, at least one substituent of the substitutedC₃-C₆₀ carbocyclic group, the substituted C₁-C₆₀ heterocyclic group, thesubstituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group,the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxygroup, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₂-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group is selectedfrom: deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, and a terphenylgroup; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, a terphenyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂), Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ areeach independently selected from hydrogen, deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryl group substituted with a C₁-C₆₀ alkyl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and * and *′ each indicate a binding siteto a neighboring atom.
 10. The condensed cyclic compound of claim 9,wherein, L₁, L₁₁, and L₁₂ are each independently selected from: *—O—*′,a benzene group, a pentalene group, an indene group, a naphthalenegroup, an azulene group, a heptalene group, an indacene group, anacenaphthalene group, a fluorene group, a spiro-bifluorene group, aspiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group; a benzenegroup, a pentalene group, an indene group, a naphthalene group, anazulene group, a heptalene group, an indacene group, an acenaphthalenegroup, a fluorene group, a spiro-bifluorene group, aspiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group, eachsubstituted with at least one selected from deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂), and Q₁ and Q₃₁ to Q₃₃ are each independently selected froma C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, and a pyridinyl group. 11.The condensed cyclic compound of claim 9, wherein, L₁, L₁₁, and L₁₂ areeach independently selected from *—O—*′ and groups represented byFormulae 3-1 to 3-29:

wherein, in Formulae 3-1 to 3-29, Y₁ is selected from C(Z₃)(Z₄), N(Z₅),Si(Z₆)(Z₇), O, and S, Z₁ to Z₇ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a benzofuranyl group, a benzothiophenyl group, a benzosilolylgroup, a dibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), Q₃₁ to Q₃₃ areeach independently selected from a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a biphenyl group, a terphenyl group, a naphthylgroup, and a pyridinyl group, d2 is an integer from 0 to 2, d3 is aninteger from 0 to 3, d4 is an integer from 0 to 4, d6 is an integer from0 to 6, d8 is an integer from 0 to 8, and * and *′ each indicate abinding site to a neighboring atom.
 12. The condensed cyclic compound ofclaim 9, wherein, a1 is 1 or
 2. 13. The condensed cyclic compound ofclaim 9, wherein, Ar₁ and Ar₂ are each independently selected from: aphenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, an adamantanylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a triazinyl group, a thiophenyl group, a furanylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, a dibenzosilolyl group, a benzonaphtho silolylgroup, a dinaphtho silolyl group, a benzimidazolyl group, aphenanthrolinyl group, and an imidazopyridinyl group; a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a triphenylenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, an adamantanyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a thiophenyl group, a furanyl group, a quinolinylgroup, an isoquinolinyl group, a benzofuranyl group, a benzothiophenylgroup, a dibenzosilolyl group, a benzonaphtho silolyl group, a dinaphthosilolyl group, a benzimidazolyl group, a phenanthrolinyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, a heptalenyl group,an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, an adamantanylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a triazinyl group, a thiophenyl group, a furanylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, a dibenzosilolyl group, a benzonaphtho silolylgroup, a dinaphtho silolyl group, a benzimidazolyl group, aphenanthrolinyl group, an imidazopyridinyl group, —N(Q₃₁)(Q₃₂),—Si(Q₃₁)(Q₃₂)(Q₃₃), and —P(═O)(Q₃₁)(Q₃₂); and —N(Q₁)(Q₂), —B(Q₁)(Q₂),—S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), and Q₁, Q₂, and Q₃₁ to Q₃₃ are eachindependently selected from a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group,and a pyridinyl group.
 14. The condensed cyclic compound of claim 9,wherein, Ar₁ and Ar₂ are each independently selected from groupsrepresented by Formulae 4-1 to 4-15:

wherein, in Formulae 4-1 to 4-15, Y₃₁ is selected from C(Z₃₄)(Z₃₅),N(Z₃₆), Si(Z₃₇)(Z₃₈), O, and S, Z₃₁ to Z₃₈ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, a phenyl group substituted with a C₁-C₂₀ alkyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃), Q₃₁ to Q₃₃ are each independently selected from aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, abiphenyl group, a terphenyl group, and a phenyl group substituted with aC₁-C₂₀ alkyl group, e3 is an integer from 0 to 3, e4 is an integer from0 to 4, e5 is an integer from 0 to 5, e6 is an integer from 0 to 6, e7is an integer from 0 to 7, e15 is an integer from 0 to 15, and indicatesa binding site to a neighboring atom.
 15. The condensed cyclic compoundof claim 9, wherein, R₅ to R₁₄ are each independently selected from: agroup represented by Formula 2, a phenyl group, a biphenyl group, aterphenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, apyrenyl group, a triphenylenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, an adamantanyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a thiophenyl group, a furanyl group, a quinolinyl group, anisoquinolinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzosilolyl group, a benzonaphtho silolyl group, a dinaphtho silolylgroup, a benzimidazolyl group, a phenanthrolinyl group, and animidazopyridinyl group; a phenyl group, a biphenyl group, a terphenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, atriphenylenyl group, a chrysenyl group, a naphthacenyl group, a picenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a rubicenyl group, a coronenyl group, an ovalenylgroup, an adamantanyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a triazinyl group, a thiophenylgroup, a furanyl group, a quinolinyl group, an isoquinolinyl group, abenzofuranyl group, a benzothiophenyl group, a dibenzosilolyl group, abenzonaphtho silolyl group, a dinaphtho silolyl group, a benzimidazolylgroup, a phenanthrolinyl group, and an imidazopyridinyl group, eachsubstituted with at least one selected from deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a triphenylenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, an adamantanyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a thiophenyl group, a furanyl group, a quinolinylgroup, an isoquinolinyl group, a benzofuranyl group, a benzothiophenylgroup, a dibenzosilolyl group, a benzonaphtho silolyl group, a dinaphthosilolyl group, a benzimidazolyl group, a phenanthrolinyl group, animidazopyridinyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and—P(═O)(Q₃₁)(Q₃₂); and —B(Q₁)(Q₂), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), andQ₁, Q₂, and Q₃₁ to Q₃₃ are each independently selected from a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, and a pyridinyl group.
 16. Thecondensed cyclic compound of claim 9, wherein, in Formula 1-1, i) R₁ toR₄ and R₉ to R₁₀ are each hydrogen, or ii) R₁ to R₄ are each hydrogen,and R₉ to R₁₀ are linked to form a benzene group.
 17. The condensedcyclic compound of claim 9, wherein, in Formula 1-2, i) R₁ to R₄ and R₉to R₁₂ are each hydrogen, ii) R₁ to R₄ and R₉ to R₁₀ are each hydrogen,and Ru and R₁₂ are linked to form a benzene group, or iii) R₁ to R₂ andR₉ to R₁₂ are each hydrogen, and R₃ and R₄ are linked to form a benzenegroup or a pyridine group.
 18. The condensed cyclic compound of claim 9,wherein, i) R₅ is a group represented by Formula 2, and R₆ to R₈ areeach hydrogen, ii) R₆ is a group represented by Formula 2, and R₅, R₇,and R₈ are each hydrogen, iii) R₇ is a group represented by Formula 2,and R₅, R₆, and R₈ are each hydrogen, or iv) R₈ is a group representedby Formula 2, and R₅ to R₇ are each hydrogen.
 19. The condensed cycliccompound of claim 9, wherein, the condensed cyclic compound is selectedfrom Compounds A105 to A119 and B105 to B119: